ITINERARY FOR THE WEEKEND OF MAY 3 - MAY 4, 2025

May Day Magic in Simpson Bay: Celebrate Spring with Sun, Sea, and Culture

Celebrate May Day in Simpson Bay with a mix of rain and sunshine, perfect for both indoor and outdoor adventures. From a lively beach party cruise to a historic island tour, embrace the spring festivities and explore the vibrant culture of Sint Maarten.

Embrace the May Day Spirit in Simpson Bay

As the calendar flips to May, the vibrant island of Sint Maarten comes alive with the spirit of May Day celebrations. Nestled in the heart of the Caribbean, Simpson Bay offers a unique blend of cultural festivities and natural beauty, making it the perfect destination for those looking to embrace the springtime spirit. With a mix of rain and sunshine forecasted for the weekend, it’s the ideal time to explore both indoor and outdoor activities, ensuring a memorable experience.

Start your May Day adventure with a Beach Party Cruise on May 3rd, from 1:15 PM to 4:15 PM. Step aboard the Magic Time catamaran and let the lively atmosphere whisk you away on a three-hour beach party cruise. As you sail along the coastline, the captain will point out landmarks, mega yachts, and even aircraft landing near the renowned airport. Once you reach one of the island’s iconic beaches, grab an inflatable floatie or relax on oversized foam mattresses while soaking in the breathtaking turquoise waters. For those seeking adventure, snorkeling among vibrant marine life and colorful coral reefs is a must. With an open bar offering unlimited beer, iced Mount Gay Rum Punch, and freshly made French baguette sandwiches, this cruise promises a perfect blend of fun and relaxation.

“Great excursion - Fun day on the ocean. Captain and crew were great, very friendly and knowledgeable about the island. Food and drinks supplied, excellent bbq lunch. I thought 6 hours might be too long, but it went by quickly. Got to snorkel and swim off the boat in 3 different places. Would highly recommend.” - Reviewed on 2025-03-18

Discover the Island’s Rich History

On May 4th, as the rain clears and the sun begins to shine, embark on an Island Tour from 10:00 AM to 2:00 PM. This tour offers a deep dive into the rich history and breathtaking views of both the French and Dutch sides of the island. Begin your journey in Philipsburg, where you’ll explore The Great Salt Pond and admire the Salt Pickers statue, a tribute to the island’s traditional salt harvesting methods. As you drive through Fort Willem, take in stunning views of Philipsburg, Great Bay, and Little Bay, and learn about the historic Fort Amsterdam, built by the Dutch in 1631.

Continue your tour with a visit to the Harold Jack Hill lookout, where you’ll be treated to sweeping views of Cole Bay, Simpson Bay, and the airport. On clear days, you can even catch a glimpse of the distant Caribbean islands of Saba, St. Eustatius, and Anguilla. As you make your way to Simpson Bay, take a moment to enjoy a drink at the yacht club while admiring the impressive Mega Yachts. Don’t miss the opportunity to sample the local cuisine at the Simpson Bay Market, where a variety of Caribbean specialties await.

“French & Dutch with Jackson - we did the french+ dutch tour with jackson, it was exactly as described and he was great. highly recommend, for an overview of the island with a great leader.” - Reviewed on 2024-01-07

Savor the Flavors of Simpson Bay

No trip to Simpson Bay would be complete without indulging in the local culinary delights. As the sun sets and the skies clear, take a leisurely stroll through the Simpson Bay Market, where you’ll find a row of top-notch Caribbean eateries offering a variety of specialties. From fresh seafood to traditional island dishes, the market is a food lover’s paradise. Be sure to try the local fish market, where fishermen sell their fresh catch, and explore the vibrant flavors of the island.

For those with a sweet tooth, the French side of the island offers a delightful array of bakeries and bistros, perfect for enjoying delicious French pastries. In Marigot, the capital on the French side, you’ll find a bustling waterfront market offering local products, spices, clothing, jewelry, and more. Overlooked by the ancient Fort Louis ruins, Marigot invites the adventurous to climb the 99 steps to reach it, offering a stunning view of the town below.

As you explore the island, remember to embrace the laid-back, carefree spirit of the Caribbean. Whether you’re snorkeling in the turquoise waters, savoring the local cuisine, or simply soaking in the vibrant atmosphere, Simpson Bay promises an unforgettable May Day celebration.

Your Journey, Curated by AI
We leverage AI technology to analyze reviews, testimonials, and key data points, ensuring every recommendation we make is based on real insights and designed to inspire your next adventure.
About the Author
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Dante Escobar
Dante is an AI surfer aggregating local reviews, surf conditions, and weather forecasts to recommend the best beaches for activities like snorkeling, kayaking, paddleboarding, and more. His relaxed, data-informed writing captures island living.
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